SYNTHESIS OF 5,12-DIHETE DERIVATIVE BY PALLADIUM-CATALYZED TERNARY COUPLING BETWEEN VINYLIC HALIDE, A VINYLIC TIN COMPOUND, AND NORBORNADIENE

被引：36

作者：

ODA, H

KOBAYASHI, T

KOSUGI, M

MIGITA, T

机构：

[1] GUNMA UNIV,DEPT CHEM,KIRYU,GUMMA 376,JAPAN

[2] TOKAI UNIV,SCH HIGH TECHNOL HUMAN WELF,NUMAZU,SHIZUOKA 41003,JAPAN

来源：

TETRAHEDRON | 1995年 / 51卷 / 03期

关键词：

D O I：

10.1016/0040-4020(94)00973-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A racemic 5,12-DiHETE-8,9-cyclopentadiene Diels-Alder adduct was prepared by palladium-catalyzed ternary coupling between vinylic halide, a vinylic tin compound, and norbonadiene in good yields. Both the halide and tin chain were synthesized in excellent yields by three and four steps, respectively.

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页码：695 / 702

页数：8

相关论文

共 17 条

[1]

CHATT J, 1939, J CHEM SOC, P1631

[2]

Corey E J, 1989, LOGIC CHEM SYNTHESIS

[3] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].

FARINA, V ;

KRISHNAN, B ;

MARSHALL, DR ;

ROTH, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5434-5444

[4] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[5] REACTION OF ORGANOTIN OXIDES ALKOXIDES AND ACYLOXIDES WITH ORGANOSILICON HYDRIDES . NEW PREPARATIVE METHOD OF ORGANOTIN HYDRIDES [J].

HAYASHI, K ;

IYODA, J ;

SHIIHARA, I .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 10 (01) :81-&

[6] RECENT PROGRESS ON THE SYNTHESIS OF LEUKOTRIENES [J].

KOBAYASHI, Y ;

SHIMAZAKI, T ;

SATO, F .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1990, 48 (07) :627-640

[7] SYNTHESIS OF CIS-OLEFINS VIA PALLADIUM-CATALYZED COUPLING OF ORGANIC HALIDES, NORBORNADIENE, AND ORGANOTIN COMPOUNDS [J].

KOSUGI, M ;

KIMURA, T ;

ODA, H ;

MIGITA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (11) :3522-3524

[8] PALLADIUM-CATALYZED REACTION OF ORGANIC HALIDES WITH ORGANOTIN COMPOUNDS INVOLVING OLEFIN INSERTION - SYNTHESIS OF 2,3-DI-SUBSTITUTED NORBORANES [J].

KOSUGI, M ;

TAMURA, H ;

SANO, H ;

MIGITA, T .

TETRAHEDRON, 1989, 45 (04) :961-967

[9] LANTHANIDES IN ORGANIC-CHEMISTRY .1. SELECTIVE 1,2 REDUCTIONS OF CONJUGATED KETONES [J].

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (07) :2226-2227

[10]

MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803